CA2696261A1 - Nouveaux composes - Google Patents
Nouveaux composes Download PDFInfo
- Publication number
- CA2696261A1 CA2696261A1 CA2696261A CA2696261A CA2696261A1 CA 2696261 A1 CA2696261 A1 CA 2696261A1 CA 2696261 A CA2696261 A CA 2696261A CA 2696261 A CA2696261 A CA 2696261A CA 2696261 A1 CA2696261 A1 CA 2696261A1
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- general formula
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- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 159
- 239000000203 mixture Substances 0.000 claims abstract description 128
- 150000003839 salts Chemical class 0.000 claims abstract description 46
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 37
- 150000007524 organic acids Chemical class 0.000 claims abstract description 22
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 383
- 238000000034 method Methods 0.000 claims description 142
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 29
- 208000002193 Pain Diseases 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 208000004296 neuralgia Diseases 0.000 claims description 5
- 230000002757 inflammatory effect Effects 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 3
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- 208000021722 neuropathic pain Diseases 0.000 claims description 3
- 208000027109 Headache disease Diseases 0.000 claims description 2
- 206010045171 Tumour pain Diseases 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 208000005298 acute pain Diseases 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 210000000929 nociceptor Anatomy 0.000 claims description 2
- 208000009935 visceral pain Diseases 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 104
- 238000004128 high performance liquid chromatography Methods 0.000 description 91
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 72
- 230000014759 maintenance of location Effects 0.000 description 70
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 40
- 229910001868 water Inorganic materials 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- -1 R5 denotes H Chemical group 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000002585 base Substances 0.000 description 25
- 239000002904 solvent Substances 0.000 description 24
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000002953 preparative HPLC Methods 0.000 description 18
- 239000012071 phase Substances 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 14
- 238000001514 detection method Methods 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 229910021529 ammonia Inorganic materials 0.000 description 11
- 235000019253 formic acid Nutrition 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 235000011181 potassium carbonates Nutrition 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000012280 lithium aluminium hydride Substances 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 150000001735 carboxylic acids Chemical class 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 235000019759 Maize starch Nutrition 0.000 description 5
- 208000006673 asthma Diseases 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
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- WYVFPGFWUKBXPZ-UHFFFAOYSA-N tert-butyl n-(4-oxocyclohexyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CCC(=O)CC1 WYVFPGFWUKBXPZ-UHFFFAOYSA-N 0.000 description 4
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
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- 239000012317 TBTU Substances 0.000 description 3
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 3
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- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 208000001640 Fibromyalgia Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- Oncology (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Otolaryngology (AREA)
- Obesity (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EPPCT/EP2007/058408 | 2007-08-14 | ||
| PCT/EP2007/058408 WO2008022945A1 (fr) | 2006-08-19 | 2007-08-14 | Arylsulfonamides à effet analgésique |
| PCT/EP2008/052157 WO2009021758A1 (fr) | 2007-08-14 | 2008-02-21 | Arylsulfonamides ayant un effet analgésique |
| EPPCT/EP2008/052157 | 2008-02-21 | ||
| EP08102043.0 | 2008-02-26 | ||
| EP08102043A EP2025673A1 (fr) | 2007-08-14 | 2008-02-26 | Arylsulfonamides ayant activité analgésique |
| PCT/EP2008/060562 WO2009021944A1 (fr) | 2007-08-14 | 2008-08-12 | Nouveaux composés |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2696261A1 true CA2696261A1 (fr) | 2009-02-19 |
Family
ID=40589564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2696261A Abandoned CA2696261A1 (fr) | 2007-08-14 | 2008-08-12 | Nouveaux composes |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US8394805B2 (fr) |
| EP (1) | EP2188269B1 (fr) |
| JP (1) | JP5250627B2 (fr) |
| KR (1) | KR20100055469A (fr) |
| CN (1) | CN101821245B (fr) |
| AR (1) | AR068341A1 (fr) |
| AU (2) | AU2008288431A1 (fr) |
| BR (1) | BRPI0815181A2 (fr) |
| CA (1) | CA2696261A1 (fr) |
| CO (1) | CO6331335A2 (fr) |
| EA (1) | EA201000296A1 (fr) |
| EC (1) | ECSP109978A (fr) |
| MA (1) | MA31613B1 (fr) |
| MX (1) | MX2010001664A (fr) |
| NZ (1) | NZ583815A (fr) |
| PE (1) | PE20090593A1 (fr) |
| TN (1) | TN2010000072A1 (fr) |
| TW (1) | TW200911744A (fr) |
| UY (1) | UY31287A1 (fr) |
| WO (1) | WO2009021944A1 (fr) |
| ZA (1) | ZA201008350B (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006039003A1 (de) | 2006-08-19 | 2008-02-21 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Verbindungen |
| EP2025675A1 (fr) | 2007-08-14 | 2009-02-18 | Boehringer Ingelheim International GmbH | Arylsulfonamides ayant activité analgésique |
| EA201000296A1 (ru) | 2007-08-14 | 2010-08-30 | Бёрингер Ингельхайм Интернациональ Гмбх | Новые соединения |
| US20110046106A1 (en) * | 2008-02-06 | 2011-02-24 | Boehringer Ingelheim International Gmbh | Aryl sulfonamides as effective analgesics |
| MX2011001563A (es) * | 2008-08-12 | 2011-03-04 | Boehringer Ingelheim Int | Procedimiento para la preparacion de compuestos de piperazina sustituidos con cloalquilo. |
| US8207335B2 (en) * | 2009-02-13 | 2012-06-26 | Boehringer Ingelheim International Gmbh | Process for making certain compounds having B1 antagonistic activity |
| CA2807078A1 (fr) * | 2010-08-05 | 2012-02-09 | Boehringer Ingelheim International Gmbh | Sels d'addition d'acide du 2-[2-[[(4-methoxy-2,6-dimethylphenyl)sulfonyl]-(methyl)amino]ethoxy]-n-methyl-n-[3-(4-methylpiperazine-1-yl)cyclohexyl]acetamide, et leur utilisation en tant qu'antagonistes du recepteur de la bradykinine-b1 |
| WO2012022796A2 (fr) | 2010-08-20 | 2012-02-23 | Boehringer Ingelheim International Gmbh | Nouvelles combinaisons |
| BR112013005193A2 (pt) | 2010-09-03 | 2016-05-03 | Gruenenthal Gmbh | derivados substituídos de tetra-hidropirrolopirazina |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0173552B1 (fr) | 1984-08-24 | 1991-10-09 | The Upjohn Company | Composés recombinants d'ADN et l'expression de polypeptides comme le tPA |
| IL115420A0 (en) | 1994-09-26 | 1995-12-31 | Zeneca Ltd | Aminoheterocyclic derivatives |
| MXPA02004985A (es) | 1999-11-26 | 2003-10-14 | Shionogi & Co | Antagonistas del neuropeptido y, y5. |
| FR2819254B1 (fr) * | 2001-01-08 | 2003-04-18 | Fournier Lab Sa | Nouveaux composes de la n-(phenylsulfonyl) glycine, leur procede de preparation et leur utilisation pour obtenir des compostions pharmaceutiques |
| FR2840897B1 (fr) * | 2002-06-14 | 2004-09-10 | Fournier Lab Sa | Nouveaux derives d'arylsulfonamides et leur utilisation en therapeutique |
| EP1572678A4 (fr) | 2002-12-19 | 2008-05-07 | Elan Pharm Inc | Antagonistes de la bradykinine a substitution n-phenylsulfonamide |
| CN1756551A (zh) * | 2003-01-31 | 2006-04-05 | 普雷迪克医药品控股公司 | 新型芳基哌嗪基化合物 |
| EA008921B1 (ru) * | 2003-03-25 | 2007-08-31 | Лаборатуар Фурнье С.А. | Производные бензолсульфонамидов, способ их получения и их применение для лечения боли |
| US7521457B2 (en) | 2004-08-20 | 2009-04-21 | Boehringer Ingelheim International Gmbh | Pyrimidines as PLK inhibitors |
| AU2005289881A1 (en) * | 2004-09-23 | 2006-04-06 | Amgen Inc. | Substituted sulfonamidopropionamides and methods of use |
| US20080090863A1 (en) | 2004-09-30 | 2008-04-17 | Taisho Pharmaceutical Co., Ltd. | Pyridine Derivatives and Their Use as Medicaments for Treating Diseases Related to Mch Receptor |
| DE102005013967A1 (de) * | 2004-11-05 | 2006-10-05 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Bradykinin-B1-Antagonisten, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel |
| US20060217362A1 (en) | 2004-12-29 | 2006-09-28 | Tung Jay S | Novel compounds useful for bradykinin B1 receptor antagonism |
| CA2687931C (fr) | 2007-05-31 | 2016-05-24 | Boehringer Ingelheim International Gmbh | Antagonistes des recepteurs ccr2 et utilisations de ceux-ci |
| DE102007034620A1 (de) * | 2007-07-25 | 2009-01-29 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue B1-Antagonisten |
| EA201000296A1 (ru) | 2007-08-14 | 2010-08-30 | Бёрингер Ингельхайм Интернациональ Гмбх | Новые соединения |
| DE502008002979D1 (de) * | 2007-08-14 | 2011-05-05 | Boehringer Ingelheim Int | Arylsulfonamide mit analgetischer wirkung |
| DE102007046887A1 (de) * | 2007-09-28 | 2009-04-09 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung von (1R,5S)-Anhydroecgoninestersalzen |
-
2008
- 2008-08-12 EA EA201000296A patent/EA201000296A1/ru unknown
- 2008-08-12 KR KR1020107005536A patent/KR20100055469A/ko not_active Application Discontinuation
- 2008-08-12 JP JP2010520555A patent/JP5250627B2/ja active Active
- 2008-08-12 BR BRPI0815181 patent/BRPI0815181A2/pt not_active Application Discontinuation
- 2008-08-12 CN CN2008801116296A patent/CN101821245B/zh not_active Expired - Fee Related
- 2008-08-12 WO PCT/EP2008/060562 patent/WO2009021944A1/fr active Application Filing
- 2008-08-12 EP EP08803005.1A patent/EP2188269B1/fr active Active
- 2008-08-12 MX MX2010001664A patent/MX2010001664A/es active IP Right Grant
- 2008-08-12 NZ NZ583815A patent/NZ583815A/en not_active IP Right Cessation
- 2008-08-12 AU AU2008288431A patent/AU2008288431A1/en not_active Abandoned
- 2008-08-12 CA CA2696261A patent/CA2696261A1/fr not_active Abandoned
- 2008-08-12 PE PE2008001366A patent/PE20090593A1/es not_active Application Discontinuation
- 2008-08-12 US US12/672,460 patent/US8394805B2/en active Active
- 2008-08-13 TW TW097130828A patent/TW200911744A/zh unknown
- 2008-08-13 UY UY31287A patent/UY31287A1/es not_active Application Discontinuation
- 2008-08-13 AR ARP080103538A patent/AR068341A1/es unknown
-
2009
- 2009-02-13 AU AU2009281472A patent/AU2009281472A1/en not_active Abandoned
-
2010
- 2010-02-12 CO CO10016009A patent/CO6331335A2/es active IP Right Grant
- 2010-02-12 TN TNP2010000072A patent/TN2010000072A1/fr unknown
- 2010-02-15 MA MA32623A patent/MA31613B1/fr unknown
- 2010-02-19 EC EC2010009978A patent/ECSP109978A/es unknown
- 2010-11-22 ZA ZA2010/08350A patent/ZA201008350B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20100055469A (ko) | 2010-05-26 |
| AU2008288431A1 (en) | 2009-02-19 |
| AR068341A1 (es) | 2009-11-11 |
| US8394805B2 (en) | 2013-03-12 |
| EP2188269A1 (fr) | 2010-05-26 |
| ECSP109978A (es) | 2010-03-31 |
| BRPI0815181A2 (pt) | 2015-03-31 |
| PE20090593A1 (es) | 2009-06-03 |
| MA31613B1 (fr) | 2010-08-02 |
| ZA201008350B (en) | 2011-08-31 |
| UY31287A1 (es) | 2009-04-30 |
| JP5250627B2 (ja) | 2013-07-31 |
| JP2010535839A (ja) | 2010-11-25 |
| AU2009281472A1 (en) | 2010-02-18 |
| TW200911744A (en) | 2009-03-16 |
| US20110098282A1 (en) | 2011-04-28 |
| CN101821245A (zh) | 2010-09-01 |
| CO6331335A2 (es) | 2011-10-20 |
| EA201000296A1 (ru) | 2010-08-30 |
| TN2010000072A1 (en) | 2011-09-26 |
| NZ583815A (en) | 2012-03-30 |
| CN101821245B (zh) | 2012-10-10 |
| EP2188269B1 (fr) | 2014-05-07 |
| MX2010001664A (es) | 2010-03-10 |
| WO2009021944A1 (fr) | 2009-02-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20130812 |
|
| FZDE | Discontinued |
Effective date: 20150812 |